1. Field of the Invention
The present invention relates to novel fluorine-containing compounds, and more particularly to fluorine-containing compounds having a perfluorocyclic ether group and a method of producing the same.
2. Description of the Prior Art
Heretofore, as fluorine-containing styrene derivatives, compounds represented by the following general formula: ##STR3## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group, R.sup.2 represents a hydrogen atom or a fluorine-containing group, R.sup.3 represents a fluorine-containing group, X represents --O--or&gt;Si (R).sub.2 in which R represents a lower alkyl group, Y represents a halogen atom, n is 0 or 1, and a is an integer of 0 to 4 are known (see Japanese Pre-examination Patent Publication (KOKAI) Nos. 62-104814 and 62-289538).
The above fluorine-containing styrene derivatives can be homopolymerized or copolymerized with another polymerizable monomer to introduce a fluorine-containing group into various polymers and therefore very useful industrially.
However, specifically indicated fluorine-containing groups (R.sup.2 and R.sup.3) in the above fluorine-containing styrene derivatives are a polyfluoroalkyl group or a perfluoroalkyl group having 1 to 10 carbon atoms and a branched fluorooxyalkyl group having an ether linkage represented by the following formula: ##STR4## That is, styrene derivatives having a perfluorocyclic ether group are not known at all.
Hitherto, as organic compounds having a perfluorocyclic ether group, compounds represented by the following formula: ##STR5## are known. Although these fluorine-containing organic compounds are used as an inactive liquid, the fluorine-containing compounds do not have a functional group and are poor in reactivity with other substances and therefore it cannot be expected to use the fluorine-containing compounds, for example, as a raw material for synthesis of other materials.
On the other hand, U.S. Pat. No. 4,033,984, U.S. Pat. No. 4,035,388, Japanese Patent Publication (KOKOKU) Nos. 59-42676, 60-15630, and 60-2291 disclose fluorine-containing compounds having a perfluorocyclic ether group and rich with reactivity derived from COF radical, represented by the following formula (i): ##STR6##
Further, perfluoro compounds represented by the following formulas (ii) and (iii): ##STR7## are reported (see GB Patent 1571356 A, Japanese Pre-examination Patent Publication (KOKAI) No. 53-82713).
Since all of these compounds represented by the formulas (i) to (iii) have a perfluorocyclic ether group and a reactivity, they are expected to be used as a raw material for synthesis of other compounds. However, as compounds having a perfluorocyclic ether group, compounds having an allyl group (--CH.sub.2 CH.dbd.CH.sub.2) or a group having an unsubstituted or lower alkyl-substituted stylyl group represented by the following general formula: ##STR8## wherein R stands for a hydrogen atom or a lower alkyl group, are not known.